South Side Vacation Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Browse Select South Side Vacation Homes
Our top choices for South Side vacation homes

Stylish 4BR South Loop Home State 23-202
Stylish 4BR South Loop Home State 23-202
10.0 out of 10, Exceptional, (1)
The price is CA $171
CA $553 total
includes taxes & fees
Sep 2 - Sep 3

Relax & Unwind in This Comfortable 3BR Unit
Relax & Unwind in This Comfortable 3BR Unit
10.0 out of 10, Exceptional, (4)
The price is CA $218
CA $463 total
includes taxes & fees
Sep 9 - Sep 10

Studio Apt Comfy & Sunlit
Studio Apt Comfy & Sunlit
The price is CA $127
CA $283 total
includes taxes & fees
Sep 3 - Sep 4

Hyde Park Haven | 2BR Retreat
Hyde Park Haven | 2BR Retreat
8.0 out of 10, Very good, (1)
The price is CA $190
CA $393 total
includes taxes & fees
Sep 1 - Sep 2

Contemporary 2BR Apartment in Vibrant Hyde Park
Contemporary 2BR Apartment in Vibrant Hyde Park
The price is CA $195
CA $388 total
includes taxes & fees
Sep 16 - Sep 17

Furnished 3BR Apt w/ Laundry
Furnished 3BR Apt w/ Laundry
10.0 out of 10, Exceptional, (2)
The price is CA $162
CA $380 total
includes taxes & fees
Sep 2 - Sep 3

1BR in Prime Hyde Park Apt
1BR in Prime Hyde Park Apt
The price is CA $138
CA $291 total
includes taxes & fees
Sep 16 - Sep 17

Hyde Park 1BR w/ Charm
Hyde Park 1BR w/ Charm
The price is CA $127
CA $283 total
includes taxes & fees
Sep 3 - Sep 4
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Top South Side Hotel Reviews
Find out more about South Side
Find out more about South Side
South Side Vacation Homes information
Number of reviews | 9 |
---|---|
Accommodation | 99 Vacation Homes |
Lowest Price | |
Highest Price |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Vacation Homes in Other Destinations
More Accommodation Types in South Side
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels
Flights
- Flights from Vancouver to Toronto
- Flights from Detroit to Los Angeles
- Buffalo Niagara Intl. Airport Flights
- Flights from Calgary to Dubai
- Flights from Toronto to Male
- Cheap Flights to Philippines
- Flights from Montreal to Athens
- Flights from Toronto to New York
- Flights from Edmonton
- Flights from Charlottetown to Toronto
- Cheap Flights to Thailand
- Flights from St. John's to Orlando
- Flights from Montreal to New York